1-(tert-butoxycarbonyl)-4-(9,10-dioxo-9,10-dihydro-1-anthracenyl)pyrrolidin-2-one | 844873-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-(tert-butoxycarbonyl)-4-(9,10-dioxo-9,10-dihydro-1-anthracenyl)pyrrolidin-2-one
• 英文别名: Tert-butyl 4-(9,10-dioxoanthracen-1-yl)-2-oxopyrrolidine-1-carboxylate
• CAS: 844873-58-1
• 化学式: C₂₃H₂₁NO₅
• 分子量: 391.423
• InChiKey: MJUZISYOEWNTHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(tert-butoxycarbonyl)-4-(9,10-dioxo-9,10-dihydro-1-anthracenyl)pyrrolidin-2-one 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以100%的产率得到4-(9,10-dioxo-9,10-dihydro-1-anthracenyl)pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880
• 作为产物：
  描述：

  N-Boc-3-吡咯啉 在 palladium diacetate 、 水 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.75h， 生成 1-(tert-butoxycarbonyl)-4-(9,10-dioxo-9,10-dihydro-1-anthracenyl)pyrrolidin-2-one
  参考文献：
  名称：

  Synthesis of 4-Aryl-2-pyrrolidones and β-Aryl-γ-amino-butyric Acid (GABA) Analogues by Heck Arylation of 3-Pyrrolines with Arenediazonium Tetrafluoroborates. Synthesis of (±)-Rolipram on a Multigram Scale and Chromatographic Resolution by Semipreparative Chiral Simulated Moving Bed Chromatography

  摘要：

  We report herein a new, practical, and economic synthesis of the phosphodiesterase inhibitor Rolipram on a multigram. scale as well as the synthesis of new 4-aryl pyrrolidones and beta-aryl-gamma-amino butyric acids (GABA derivatives) employing an efficient Heck-Matsuda arylation of 3-pyrroline with aryldiazonium tetrafluoroborates. Racemic Rolipram was resolved into its enantiomers using chiral simulated moving bed chromatography having the low-cost microcrystalline cellulose triacetate as a chiral stationary phase.

  DOI：

  10.1021/jo0484880